Crystal Structures of the Amide and Iminol Tautomers O-(3,5-dinitrobenzoyloxy)benzohydroxamate. A Case of a Disappearing Solvate?
Abigail L. Albright A , Lucy Collins A , John Li A , Benjamin Harris A and Jonathan M. White A B
+ Author Affiliations
- Author Affiliations
A School of Chemistry, Bio21 Institute, The University of Melbourne, Parkville 3010, Australia.
B Corresponding author. Email: whitejm@unimelb.edu.au
Australian Journal of Chemistry 69(10) 1193-1197 https://doi.org/10.1071/CH16369
Submitted: 21 June 2016 Accepted: 15 July 2016 Published: 5 August 2016
Abstract
The O-(3,5-dinitrobenzoyl) derivative of benzohydroxamic acid 1 crystallizes in its iminol tautomeric form, hydrogen bonded to a molecule of dimethyl sulfoxide (DMSO) when crystallized from methanol in the presence of DMSO. In contrast, in the absence of DMSO, 1 crystallizes in its amide tautomeric form. Computations suggest that in the absence of DMSO, the amide tautomer of 1 is significantly more stable than the iminol form. Conversely, in the presence of DMSO, the two forms have comparable stabilities. Solution infrared spectra of 1 run in dichloromethane are consistent with the amide tautomeric form predominating; however, titration of aliquots of DMSO results in the formation of a second species with spectral characteristics consistent with the iminol tautomer.
References
[1] (a) H. B. Burgi, J. D. Dunitz, E. Shefter, J. Am. Chem. Soc. 1973, 95, 5065.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXkvFWhs7w%3D&md5=d4c0ed54863b59fd0ecc7d8c32ddcfabCAS |
(b) Structure Correlation, Vols 1 and 2 (Eds H. B. Burgi, J. D. Dunitz) 1994 (Verlag Chemie: Weinheim)
(c) D. Birney, T. K. Lim, J. Peng, B. R. Pool, J. M. White, J. Am. Chem. Soc. 2002, 124, 5091.
| Crossref | GoogleScholarGoogle Scholar |
(d) B. R. Pool, J. M. White, Org. Lett. 2000, 2, 3505.
| Crossref | GoogleScholarGoogle Scholar |
(e) Y. W. Goh, J. M. White, Aust. J. Chem. 2009, 62, 419.
| Crossref | GoogleScholarGoogle Scholar |
(f) Y. W. Goh, B. R. Pool, J. M. White, J. Org. Chem. 2008, 73, 151.
| Crossref | GoogleScholarGoogle Scholar |
(g) Y. W. Goh, J. M. White, Org. Biomol. Chem. 2007, 5, 2354.
| Crossref | GoogleScholarGoogle Scholar |
(h) Y. W. Goh, S. M. Danczak, T. K. Lim, J. M. White, J. Org. Chem. 2007, 72, 2929.
| Crossref | GoogleScholarGoogle Scholar |
(i) J. Roth-Barton, Y. W. Goh, A. Karnezis, J. M. White, Aust. J. Chem. 2009, 62, 407.
| Crossref | GoogleScholarGoogle Scholar |
(j) J. Roth-Barton, J. M. White, Aust. J. Chem. 2009, 62, 1695.
| Crossref | GoogleScholarGoogle Scholar |
[2] J. S. Swenson, A. M. Davis, R. A. Deyo, B. W. Graham, E. P. Jahn, J. D. Mattice, J. Org. Chem. 1973, 38, 3956.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXlsVGksLs%3D&md5=c7d2b462e59c3d1044283ac33ca4544cCAS |
[3] (a) M. Saldyks, Z. Mielke, Spectrochim. Acta, Part A 2005, 61, 1491.
| Crossref | GoogleScholarGoogle Scholar |
(b) T. V. Surova, A. N. Enyashin, J. Struct. Chem. 2003, 44, 297.
| Crossref | GoogleScholarGoogle Scholar |
[4] (a) F. H. Allen, Acta Crystallogr., Sect. B: Struct. Sci., Cryst. Eng. Mater. 2002, 58, 380.
| Crossref | GoogleScholarGoogle Scholar |
(b) Cambridge structural database ver. 5.37. Fragment searched CC(O)NH-O with R < 5 %, no metals, 27 hits.
[5] CSD refcodes: DECJAW, DECJAW01, ERAHAG, FESPOK, MIQNEF, MIQNIJ, NEZMUA, NEZNAH, OBEKUB, SEBFUA.
[6] M. Saldyka, Z. Mielke, Vib. Spectrosc. 2007, 45, 46.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtFejurnF&md5=02a25f0887c22611eb2330c2cb766783CAS |
[7] A. I. Artemenko, E. K. Anufriev, I. V. Tikunova, O. Eksner, Zh. Prikl. Spekrosk. 1981, 33, 131.
[8] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyenger, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.04 2003 (Gaussian Inc.: Pittsburgh PA)
[9] J. Schraml, J. Sykora, P. Fielder, J. Roithova, J. Mindl, V. Blechta, I. Cisarova, O. Exner, Org. Biomol. Chem. 2004, 2, 2311.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmsVeisrw%3D&md5=4f1b733af5481567d52e542431d24b38CAS | 15305211PubMed |
[10] A. Bondi, J. Phys. Chem. 1964, 68, 441.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2cXls1Cgsg%3D%3D&md5=f7d9f8afb031c3268385a0946614665fCAS |
[11] G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Adv. 2008, 64, 112.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVGhurzO&md5=1965db3178cb384357dbea613ab9f64bCAS |
[12] L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXnt1KgsLg%3D&md5=73cc226b6a448ce22eb035dbadda41dcCAS |
[13] L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXlsVSlurk%3D&md5=0c90961ce852cc81ea6e906e41ecf184CAS |
[14] C. R. Hauser, W. B. Renfrow, Org. Synth. 1939, 19, 15.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaA1MXjvVahsQ%3D%3D&md5=3af64bd6241c162cf3cab615e6ed4455CAS |
